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The Warden

By: latinafmm2



You've been home from work for hours, it's late, you slump over to the side of the bed exhausted. You've been pounding at my holes for hours, and it seems that you just can't continue. What's wrong? I'm exhausted. I want more! Later, I'm going to go to take a nap. NO! I want more!! I said I'm going to take a nap. You roll over onto your side, and start to go to sleep. I am angry, I need more, and my fingers aren't gonna get it. I get up from the bed, and go to the dresser to get my strap out, you're not gonna get away with this, this time. I need that cock, and I need my release, and you're gonna give it to me.

I begin to lube up the dildo connected to my strap. Stroking it a few times so that it is good and lubricated, and to make sure I can feel the other side that slides inside of me. I moan softly and reach over to spread your asscheeks. You start to move and before you have the chance to do anything, I slide the toy deep into your ass, thrusting in a few times to get deeper. I moan loudly, it feels so good. You yell out, what the hell are you doing?? I just moan more and thrust deeper. I'm taking your ass. Stop, NOW! I refuse, I continue to fuck deep into you. 

You move out from under me, spanking my ass hard. I told you NO! Now you're gonna pay. You go out of the room and I can hear you on the phone. You come back into the bedroom, and throw some clothes at me. Get dressed. In a few moments there is a knock at the door, and on the other side are two police officers. They take down the information you give them, and then take me away. The charge... rape. 

You'd made it quite clear that I'm to be treated roughly, when the police had asked you if they should be extra careful with me. You told them that I had been naughty, and was to be punished for it. One of the cops is male, the other female, I'm taken to the women's side of the jail, booked quickly, and thrown into a cell with a very large, muscular looking lesbian. She smiles down at me, and grabs me by the hair, throwing me against the wall. Normally Big Bertie is in a cell by herself, but tonight I'm to be her cell-mate, and her toy. She reaches over, and grabs a stick that she in her time in her cell, has fashioned into a makeshift dildo. It is very long, and very thick, she rips my shorts from me, and slams the stick deep into my ass from behind.

She man-handles my breasts, pinching, twisting and pulling on my nipples. I scream out in pain and terror, she ignores it and so do the cops. She ravages my asshole with that stick fucking me so deep and so hard it feels like my insides are coming out when she pulls it out. My face is scratched by the wall, my hands begin to bleed from trying to push awayfrom it so that I can breath. I think I'm going to pass out, but she doesn't notice or care. I get a chance to turn my head towards the door, and there standing, watching is you, in your uniform, a slight evil smile on your face, and a glint in your eye.

You watch as this woman rapes, tortures, and beats me for hours. Finally, mercifully, I do pass out, and when I wake up, I'm in the infirmary, my hands are bandaged, my face has been attended to, and you are standing by my cot looking down at me. Your only comment is that it's not over. You have them bring me to your office. When they leave you bend me over your desk and begin to fuck me with your nightstick, telling me how naughty I've been, and that I must learn a lesson.

I shudder, and cum, I'm in pain, but the pleasure is great. You turn me around and bring in your male, and female guards, having them take me one by one. Each in turn is allowed to do with me as they wish, and may cum wherever they wish. Most though cum on my face, and force me to swallow as much of their cum as they can get down my throat. Their cocks are covered in cum, my juices, and the shit from my ass. I'm forced to clean them off, and continue to be fucked. Over and over anything that can be used as a dildo is fucked deep into me.

I'm used however they wish, and their hands smack different parts of my body. I can't imagine how many times I've been forced to cum at their hands, my screams are loud and I can't think anymore. I only feel the pain and pleasure of being used as though I'm a slut for the taking. You stand off to the side, watching, forcing one of your guards to suck your cock. When one begins to slow down you move onto the next, forcing yourself deep down her throat. I can see that they've sucked your cock before, for they do it with expertise. Finally the last of your female guards has sucked you till you're ready to cum, you pull her to her feet by her hair, turn her around, and force her to take you up her ass. I can see how your dick thrusts into her inch by inch, your face contorts as you struggle to hold your nut in long enough to get into her tight hole completely.

Her screams match mine, I look around and other female guards are sucking and being fucked by the ones that are not currently fucking me. My pussy, mouth and asshole are ravaged. I can feel another orgasm coming on. I open my mouth to scream out and a dick is stuffed in it. My screams of pleasure or muffled by the cock stuffed in my throat. I gag and choke on it, I can feel a nightstick in my pussy, and a dick in my ass. I'm on my hands and knees and I don't know how much longer I can hold myself up. I'm sinking fast. I can hear your evil chuckle as you tell them to finish me for the night. FOR THE NIGHT?!!! What does that mean?!

You ignore me and continue to give orders, as suddenly you begin to growl and cuss, cumming hard and deep into the ass of the female guard. I can feel myself slipping again. I can't hold on anymore. The last thing I feel is one last orgasm, as your guards nut all over my body. The last thing I hear is you telling them to take me back to the infirmary, that tomorrow is another night, and that I'm going to be there for a while, and they will have many chances to take me between now and then. 

The Warden



Bryan walked away for a moment and left me standing in the shower. I dried off like he told me to and sat down on a three-legged stool. Only a few minutes had gone by when he came back through the door. My massaging had me relaxed and content, but the sudden loud jerking of the door startled me. Bryan carried a box over and put it down on the desk with a thud.

"The warden wants you to wear this," he said. "You won't always have to wear this when he summons you, but tonight he's in a mood." He pulled out a pair of fishnet stockings, a garter belt, a pair of crotchless thong panties, and a long, blonde, full-bodied wig. I'll be honest; I loved where this was going.

"Is that all?" I asked, eager to hear the word "No."

"No, it's not," he said. He pulled out a pair of six-inch heels, black like the outfit, and I could only assume they were my size. The warden didn't seem like a man who would cut corners. He wanted me a certain way, and he was going to have me.

"Try all of these on. We have your measurements, so it should all be the right sizes. You will also be wearing these fake eyelashes, this red lipstick, and some other makeup." He pulled everything out of the box and put it on the table. My eyes lit up at the prospect of dressing up as a woman. I had tried cross-dressing in the past, but never as elaborate as all of this. I was excited to see what I'd look like as a sissy slut.

Before I had gone to prison that very morning, I took it upon myself to shave every inch of my body. I figured that if I was going to run into someone who was interested in me early on, I wanted to be smooth for him. I don't know why I figured my mystery dominator would want a smooth body. For all I knew he could have been interested in beefy, hairy men. In any case, I lucked out. The warden would no doubt be pleased with my smooth, raw ass.

I slipped the stockings on slowly for Bryan. He watched me as he rubbed his cock through his pants. He was already getting hard again, and the pumping he did still hadn't worn off. I loved watching that muscular beast of a man stare at me like a piece of meat. My cock was growing itself, and I bit my lip staring into his eyes from across the room.

"Can I help you while I get dressed, daddy?" I said to him. "You look like you could use a wet mouth."

"Keep getting dressed and I'll think about it," he said. He unzipped his pants and flopped his big red cock out. It was trying to stand strong under its own weight, but that thing was struggling. It bounced around as blood pumped into it, and Bryan just kept staring at me while my mouth watered.

"Yes, daddy. Whatever you say." God, I wanted his cock again so badly. I knew he had another load in his big balls for me. I would just have to wait.

With the stockings already on, I slipped on the panties and the garter belt. I hooked the clasps to the top of my fishnets and slipped my dick through the hole in the front of the panties. It certainly stood out quite a bit, but I figured the warden would probably want it that way. He had all my measurements, I'm sure he knew I was hung as well. I turned around and looked at my ass in the mirror. Goddamn I looked good. My bubble ass, freshly shaved, looked even more defined in that jet-black thong. The stockings came up and framed the bottom of my cheeks perfectly. I wiggled it back and forth, bent over and bit my lip. Bryan let out a grunt. He had begun stroking his cock again, and he was growing as big and strong as ever. I looked over at him and smiled. He just stared with those cold, lustful eyes.

I walked over to the table and picked up the heels. I was so excited to see how these looked. I slipped them on in the most feminine fashion that I could. They were incredibly sexy. I would have bought them for my ex-girlfriend if I had seen them. The warden had good taste, or so it appeared. I sat at the mirror and put on my lashes and lipstick. I was no pro, but I did a pretty good job. Then I moved to the blush and foundation. I did a good job with that too. I looked at myself in the mirror and blew myself a kiss with a wink. I was really looking like a woman from the neck up. When I slid the wig on, I was blown away. I looked damn sexy, and the wig was a perfect cherry on this slut sundae I was making.

Bryan walked over with his now rock hard cock in hand. He was silent, but he didn't have to say a word. I took his steaming hot cock in my mouth. Sitting on that stool while I sucked Bryan's perfect puffed up dick, dressed in a full sissy outfit, I fell to another level of shame and degradation. It excited me, though, so I didn't care. That was all a part of the rush; to see how much of a whore I could be. It wasn't hard to remember that not long ago I was caught covered with piss and cum with the semen of five black convicts dripping from my open asshole. Dressing like a sissy slut in prison certainly couldn't beat that.

Bryan moaned as I worked my tongue around his red-hot head. "Look at me," he said. I listened. "Open your mouth," he continued. I listened. He took two white pills and threw them in my mouth. He handed me a bottle of water and told me to swallow. I listened. "Those are vicodin. The warden wants you drugged and woozy tonight. He thinks you will be a more willing participant in his antics if you can't feel as much pain as you normally would. Don't worry; he won't leave any cuts or anything permanent on you." 

"No need to explain. I love vicodin. I can't wait until they kick in." I sucked his meat back into my mouth with a slurp and worked him hard with my hands and mouth. He let out a moan like a bear and threw his head back. I pushed his cock into my throat and held him there for a while. I gagged a few times before pulling him out and slapping my face with his dick. I was going to have to redo my makeup before this was over. My red lipstick was smeared already, and the mascara was going to run soon enough from the tears. I sucked him in again and bobbed up and down on him. He moaned louder and louder until he jerked his hips forward, ramming his beautiful dick down my throat. He filled my esophagus with his second thick load before pulling back and filling my mouth. I coughed a big cum bubble up, sucked it off my lips, and swallowed it all with a smile on my face. 

"Thank you so much for your second load, sir," I said. "Is there anything else you need?" 

"No," he said. "Just redo your makeup and get ready to go see the warden. I can see you have the sissy act down already. Keep it up. He'll like that."

"Yes, sir." I turned back to the mirror, grabbed a wet towel that Bryan handed me, and got my makeup back in order. It looked even better the second time. I was finally ready to see the warden.

Bryan stood me up and smacked me on my ass. The heels made my legs look even longer. They really brought my femininity out. I got a look at the entire image of my cross-dressed body and giggled with glee. He walked me out of the room and took me down a secluded hallway. The clicking and thudding of my heels echoed off the walls. It took me a few hundred feet to get used to the shoes, but soon I had it down. He opened up a door at the end of the hallway and instructed me through it. Suddenly I was standing in a huge room surrounded by prison cells and prisoners. I stopped for a moment, horrified and embarrassed. All of these men were about to see me in full dress, makeup and all. This may not have been the best way for me to show up to prison, but I was in it for the long haul, so I bit the bullet and walked on.

The room erupted in laughter, hoots and hollers, and the sound of hands, books and all sorts of things hitting the heavy steel bars holding back these savage men. I was happy for the bars. These men would have probably stormed out of their cells and raped me a hundred times before anybody could stop them. Some of them were big, burly men; some of them were smaller and less so. I looked at the wall of cell doors and noticed that plenty of them had their cocks in their hands. They swung them around with vigor as they shouted about my ass and what they wanted to do to me. My mouth was watering at some of them. I couldn't help it. Plenty of them were good-looking men with big cocks. The slut in me wanted their meat, but tonight I was the warden's, so I kept my mouth shut and walked on.

"Look at this little sissy faggot! I can't wait to catch you in the shower," one man yelled. I giggled at the prospect. The showers were something I looked forward to a great deal.

"Come suck the cum outta my balls, whore," another man shouted. "I got a ten-day load for you!" Little did he know, I already had a belly full of cum. Or maybe he did know, and that's why he yelled it. Surely I wasn't the first person to be fucked so relentlessly by my escort, Bryan. The rumors were probably already circulating.

"The warden's got a new toy, boys! Keep your cocks ready, it's gonna be a fun week," a third man yelled. He held his huge cock in his hand and stroked it while he yelled. I wasn't sure what he meant by "fun week," but I relished the thought. I hope he gets a piece of me soon. He had that big, bald, monster-of-a-man look to him. My mouth was watering more now, and my cock had begun to stand tall through the crotchless panties. The prisoners noticed and made sure to announce it to each other. 

At the end of the hall Bryan opened another door and pushed me through. I climbed a huge set of stairs and we stopped at the door at the top. The word "Warden" was plastered to the big wooden door, and my heart began to race. This was the moment that Bryan had been preparing me for all night - a preparation that including sodomy, penis pumps, nightsticks, relentless fucking, and not one, but two big loads of cum from his balls. The warden had ordered it all (except that last blowjob, I think Bryan took that for himself), and this was the man I was about to meet. The door swung open and we walked inside.

The office was incredibly lavish compared to the rest of the prison. I suppose it made sense. Clearly this warden ruled with no question to his power. He had me fucked by a guard and prepared for his pleasure the moment I arrived. A fire was roaring in the fire place, an entire wall of books loomed over one side of the room, a beautiful mahogany desk with a gold-plated lamp sat in front of a huge leather chair, and every other cliché addition you could make to a rich man's study decorated the room. The warden even spun around in his desk chair with a cigarette in a long-stem holder. He wore a robe and nothing else. He was muscly and good-looking, but a bit older than Bryan. He had salt and pepper hair, and an incredibly hairy body. I was turned on already, but after seeing that the warden wasn't some fat slob or hideous chud, a lot of my nerves left me, and I relaxed in my heels and garter.

"Thank you, Bryan," the warden said. "You may leave her."

"Her." That was strange, but I liked it. Tonight was going to be one hell of a fetishist's dream, I could tell that already. Bryan turned and left without a word. I stood there looking at the man splitting me open with his eyes. He stood up and put the cigarette out. His big cock fell through the split in his robe. I licked my lips, but I dare not move. I was going to let him instruct me in everything.

"I've heard a lot about you," he said. "I've been paying close attention to your case. I even went out of my way to have you brought to this prison in particular. I'm sure you noticed it happens to be out of the state you were arrested in. That's no coincidence. While you're here, there are rules to follow. I'm sure Bryan already informed you of those." I nodded. "You will address me as Sir, Warden, or Daddy. When I call for you, you will drop everything, including any cocks in your ass or mouth, and come to my office. I don't care who is inside of you; you pull them out and leave. You shouldn't get any trouble in that regard. The guards will take care of your escorts. I had you dressed tonight because I love submissive sluts, and since we can't get female prisoners, this is the next best thing to having a woman to fuck with. I am loyal to my wife, so I don't sleep with women other than her, but she doesn't know a thing about what goes on here at my prison, and she never will." 

I nodded again. "Yes, sir."

"Now," he continued, "to start, come lay on the rug in front of the fire. While you're here tonight you will make your voice higher, and make yourself as feminine as possible. Everything you do should be girly. You're my sissy slut, and you will put on the act. Do you understand?"

"Yes, daddy," I said with seductive eyes. The eyelashes and makeup certainly made it more effective. I strolled over to the rug in my most womanly walk, bouncing my butt back and forth while I looked into his eyes. He smiled and bit his lip. I noticed a rush of blood pump into his limp dick, making it bounce once or twice. I giggled and made my way. As I lay down, I poked my ass up at him and wiggled it around. "What's next, daddy?"

"Mmm. You look good. Put on a show for me, Samantha."

"Is that my name tonight, daddy?"

"Yes it is. That will be your sissy name forever, so get used to it. Any time you are dressed, you are Samantha."

"Yes, sir!" He pulled a chair over and put it down, his big robe opening wide with his stride, revealing his hairy, muscular body. I was so horny already, and the vicodin was kicking in, so I had all sorts of feelings rushing through my body. I wanted to please my master as I'd already done once tonight, so I gave it my all. I struck poses, smacked my round booty, spread my cheeks, and talked dirty to him.

"Give me a dance," he ordered. I gladly entertained the idea for him. I had never done a strip tease, but I was happy to try tonight. I assumed I would be pushing all sorts of boundaries today. I walked over to him in my outfit, my now hard dick showing clearly, bouncing around. The image must have been hot to him, because he bit his lip again and stroked his cock a few times. I bent over in front of him and shook my ass like my girlfriend always used to do for me. I danced a little bit with it before pushing it against his face. He took a big bite out of my cheek and smacked the other.

"Oh, daddy," I said in my most girlish voice. I continued my dance as he put his hands all over me. My dick was rock hard now, and he grabbed it and squeezed.

"You have a nice cock. I hope you know I'll be playing with this tonight as well. You may be fully dressed, but you'll find soon that I have my own personal tastes for fetishes. I like my cross-dressers with big cocks, not little embarrassments." Without another word he took my dick in his mouth and squeezed my big ass cheeks. My eyes rolled in the back of my head with ecstasy. He sucked me so well I thought I might burst already, but the vicodin came on in a wave and the sensation was dulled. He kept sucking on me, and I moaned like a girl for him. What an interesting concept that was; having my dick sucked while I moan like a girl.

Once he had his fill, he let my cock fall from his lips and picked up his own big cock. I took the hint and got down on my knees, my big heels sticking out from under my round butt as I squatted like a woman in front of him. I took his hairy dick into my mouth and teased him a bit while I looked at him. I batted my lashes at him with his head in between my lips, my tongue flicking the underside of his meat. He moaned and looked back at me. I started to bob my head up and down on him with my tongue still flicking back and forth. He opened up a small bottle of poppers and stuck it under my nose.

"Take three big deep breaths, and don't you dare stop sucking." I did as I was told, and the rush to my head had me spinning. The vicodin and poppers combined put me in such a state. My head was hot and full of filthy thoughts. The heat washed over my body as I swallowed his meat all the way down my throat. He moaned like a beast and threw his head back as I continued to make the swallowing motion with my throat with him inside my neck. I moaned on his dick too, giving him even more of a rush of sensation. As I pulled my head back, his cock slipped out shiny and plopped onto his hairy stomach.

"Holy fuck. Do that again, now," he commanded me. Of course I did it again. I loved doing it, and I had to make sure my first impression was a good one. This man was going to decide how my time in prison was spent. Satisfying his primal urges was the least I could do. Over and over I took him down my throat and hummed on his cock. The noises he made were enough of a reward for the act. 

The poppers soon wore off, but the vicodin was hitting me so hard my eyes were getting heavy. I kept forgetting that I was in total dress, but every time I remembered, my cock twitched with excitement while my asshole puckered. I knew it would be a fetish I would keep up with after I got out of prison.

After I did my slutty duty with my mouth, the warden stood up and dropped his robe. I sucked his cock back in between my lips a few times before he walked across the room. I dare not move without orders from him, so I sat there licking the slobber off my chin and face. 

"Now the real fun begins," he said from behind me. I turned to look at what he meant, and he was absolutely right. The real fun was getting started. He unveiled a fucking machine with one of the biggest dildos I had ever seen. It was about the size of Deyron's big cock, or maybe Bryan's pumped up shlong, but it was big nonetheless. "Come over here and position yourself on your hands and knees in front of it."

I stood up without skipping a beat and walked over to the machine. He powered it on to show me the raw power it had. Unlike any man, this thing was capable of delivering the same length and power in every thrust for as long as I (or the warden) desired. I was excited at the prospect. I got my girly ass down on all fours and poked my butt in the air. He turned a knob on the machine and it slowed to a stop. He grabbed a huge tub of anal lube and grabbed a whole handful of it. He lubed up the machine and tore my panties down. The lube was running down my cheeks and legs in no time. He left everything on but the panties and used the rest of the lube from his hands to shine my asshole up nicely. I was reeling from the opiates, and ready for another popper. I figured I would need one if I were going to take that horse cock in my hole. Sure, Bryan loosened me up, but something that size was going to hurt, no matter how warmed up I was. Like he read my mind, the warden came over with the poppers and held them under my nose while he put his fingers inside my hole. I moaned and giggled, like I knew he loved, and pushed my eager butt back against his knuckles. He had four fingers inside me in no time, and I was feeling full again. I figured he would just put his whole hairy fist inside me, but he didn't. He fucked my hole with his fingers for a while and positioned the dildo at my ass. I was ready for that familiar pressure in my abdomen; the feeling of being displaced from the inside out. I wanted it again. It was becoming an addiction. The head of the dildo slipped in as I pushed back. I slid every inch into my rectum and shouted "Oh, fuck, daddy, I love your big cock in my pussy!"

"That's right, you little cunt. Take that huge mast. You better be ready. I'm turning this thing on."

He slowly turned the knob on the machine and it started to slowly go in and out of me. Every inch, slowly slipping between my cheeks, into my sphincter muscles, testing my limits. The power increased, and so did the speed. Faster, deeper, harder. Before long, the machine was running full bore. The feeling was unbelievable. I had never been fucked so hard before, and with such a huge dildo I was full to bursting. The rumbling of the machine drowned out the sloppy noises, but I could hear my asshole singing. 




The Warden



Without warning, while I had my head down in my hands, unaware of my master's presence, he came over and tied me to the floor. My wrists were tied to two small clasps in the wood, and he threw a soft rope over the back of my knees to hold my bottom in place.

"What are you doing, daddy?" I asked him. He slapped me in the face, hard, and told me to shut up. I wasn't to ask any more questions. I listened, of course. The vicodin may have been helping with some of the pain, but being slapped in the face hurt regardless. I shut my mouth for a moment, only to have it forced open with his cock. While the machine kept up its relentless obliteration of my insides, I sucked on his cock with everything I had. The harder I sucked, the less the dildo seemed to hurt. Not that the pain was unbearable, I love some pain, but it helped balance out the sensations. He stuck the popper bottle under my nose again, and I took five deep breaths. The fumes helped with my asshole a lot, and suddenly the pleasure was through the roof. I sucked and sucked as I became more and more content with my abuse.

The warden turned around and showed me his asshole. He had been wearing a buttplug the entire time, and he instructed me to remove it with my mouth. I gladly did, but first I licked around his asshole with a strong tongue. I figured he wouldn't mind. Finally I grabbed the plug with my teeth and began to pull. It was bigger than I thought it would be, but it came out with a pop, and his hairy asshole hung open, staring me in the face. I dropped the plug and took a whiff of his insides. He had cleaned himself out perfectly, because all I could smell was musk and sweat. I stuck my tongue inside his hole as it closed, flicking back and forth inside of him. The machine kept working my hole, and I did the same for the warden's. By now my makeup had begun to run from the sweat and tears. I looked like a bonafide whore now, and I loved the idea of it.

"Oh, fuck yes, you little whore. Suck daddy's asshole. That's right." I giggled at his pleasure, happy to be his whore for the night. He spoke while I kept sucking on his hole. "I have some friends coming in tonight. They're right on the other side of that door. There are five of them, and they will all cum on you. They'll cum on your face, in your hair, on your back, on your ass, and even inside of your asshole. You will suck them, and that's it, no more. Your ass will stay on this machine while you pleasure them, and I will watch from my chair while I pump up my cock. You're going to be so loose by the time we're done that I'll need to be as big as I can be. Stay right there, cunt, and get ready for some cum. I want you covered in semen when I finally take my time with your holes."

He walked over to the door and let the men walk in. There were three black men and two white men, and they were all hung like gods. They stood single file in front of my face and fed me their cocks. One by one I sucked on them with nothing but my mouth to work with. The machine was still assaulting me through all of it. The men never said a word outside of moans and groans, but they all gave me their hot cum. The first man fucked my throat until he shot a load into my lungs, then pulled out and shot the rest on my face. I coughed up his cum in a big bubble and swallowed it like I should. The second man beat me in the face with his big meat first, abusing me, mocking me, showing me how defenseless I was. I sucked on him with a smile on my face, happy to be degraded by these alpha dicks. The third man came up with his flaccid dick and popped it into my mouth. I sucked him down and let him grow hard in my throat, then began to bob my head up and down. The precarious position I was in - my hands tied to the floor, legs strapped down, and a forearm still fucking my asshole - made giving head a little difficult, but I did it all for the warden and the men using me. It was only right that I give them my all. I occasionally looked over at the warden while I sucked on them, watching him pump his cock to a huge size. I was eager to have him inside me again, whichever hole that may be. The third man pulled out and came on my asshole and the dildo. His hot cum helped lube me up a bit and relieved my hole. The last two men came to me at the same time. One of them fucked my face while the other grabbed my cock. He smacked it around, stroked it, squeezed it, and played with it to his heart's content. The extra sensation was intense, and the man fucking my face was just as much. Soon the man in my mouth pulled out and came on my ass cheeks. His load was huge, and he glazed my big cheeks well. I just wished I could have seen all of those loads erupting from their balls. The last man had apparently been stroking himself, because he came shortly after the fifth man with no coaxing from my mouth. He shot a huge load all over my back, flicked the last drops of it on me, and they all got up and left the room. The machine still demolished my insides, and I was lightheaded at that point, but the warden knew how to wake me up. 

"I hope you know this is being recorded," he said. I snapped back to reality. "If you behave while you're here, and do everything I say, these videos will only ever be for me. If you decide to get resistant and start to refuse your duty at this prison, the whole world will see these videos." I nodded in agreement, as if I had any choice. "Good slut."

He pulled his massive red cock out of the pump, turned the machine off, untied me, and pushed me off the dildo. My ass hung open about 4 inches across, red and dripping fluids. I moaned like a whore and laughed at the sounds it made as it tightened up again. It made that slow, slick sound of fluids and flesh tightening up. My cock was dripping with lube and hard as a rock still. Despite the exhaustion I already felt, I was ready for whatever came next.

He walked over to me with a sort of strap-on I had never seen before. He strapped it to my face, and all sorts of sick thoughts ran through my head. I lay on my back in anticipation with this huge dildo dangling from my chin. He grabbed some lube from the bucket and lubed up the shlong. Then he stood over me and squatted his hole onto the end of it. He pushed hard and slid all the way down. His hairy ass came closer to my face, his hole stretched wide on the rubber cock. His huge cock and balls rested on my chest as the last inch went inside him. The heat from his meat was intense, and I loved feeling it on me. It was so primal and raw, that huge dick and balls hanging low. The image of his asshole stretched wide and his big red meat dangling around made my cock twitch. 

Once he was acclimated he started to fuck himself with the fake cock strapped to my face. The sound and sight of it was beautiful. He went up and down on that thing with purpose. Each time he pulled up his cock would swing back and forth, usually coming back to collide with the dildo. He moaned and groaned in pleasure, giving me the perfect view. Before long he bent over and took my cock in his mouth. He sucked me hard and made a ton of slobber in the process.

"Fuck my throat," he said. My garter and stockings still adorning my smooth body, I began to pump my cock into his throat while he bounced his asshole on the dildo. We stayed like that for a few minutes, me fucking his throat, and him fucking himself with my well-equipped face. I had never experienced anything like it. I had never even seen anything like it. He certainly had what he liked. Then, without moving, he grabbed the arm of the fucking machine and repositioned it so it was lower to the ground. He shoved it back in my ass, cranked up the power, and we continued our sick, sloppy endeavor. My asshole was being split open while he sucked my dick. His big meat rested on my chest as he fucked his hole. The fluids from his ass and lube had begun to drip down the strap-on and accumulate on my face. Now I was covered in cum, ass juice, sweat, and musk. It was so fucking hot and filthy I almost came, but he pulled his mouth off my cock before I did. He grabbed my balls and squeezed them hard.

"You got a big load in there for me, whore?"

I spoke muffled through the strap-on. "Yes, sir. I do. Bryan got me all ready for you, daddy."

"Mmm, fuck yes. I'm gonna get that load soon enough."

"Whenever you desire, sir."

We finally finished our twisted activity and he rolled off of me. He took the strap-on off and flopped his dick and balls onto my waiting face. He took my throbbing cock and squeezed the base while he smacked the shaft and head around hard. He beat up my dick like it had done something wrong, but it only made it bigger and harder. I sucked and licked his ballooned dick and balls, as I knew he wanted, and basked in the smell. His asshole still hung open, so I licked and spit on it here and there. He suffocated me a bit at times, but he always pulled off when necessary.

Now the warden was ready to cum. I could tell from his moans. They had grown more rabid and intense. He got down on all fours in front of the fucking machine and put the end of it inside him. Without him asking I got up and turned it on for him. He didn't quite like the full power, so I turned it down a bit so he could feel more pleasure. Not everyone can take an assault like me.

"Come lay down in a 69 with me. I want you to suck my swollen cock until I give you my load. I'll be sucking your dick as well, and if you do it right we can cum at the same time. I want to shoot my load down your throat while you do the same. We will swallow every drop, just like god intended."

I scooted down under him and took him in my mouth. The machine was working its magic on his butthole while I worked my own on his cock. He was very big, and I tried as hard as I could to take all of him, but it was hopeless. That didn't stop me, though. I worked my mouth and tongue on his cock just as I always had. The softness of the meat made it easy to swallow inch my inch. It was like working a giant worm down my throat. I sucked and slurped and swallowed him, his giant, engorged balls resting on my nose and eyes. He took me in his mouth and down his throat immediately. I fucked his face a little bit, like I knew he wanted, and continued my work. He slid the chinstrap dildo into my ass and left it there. I guess he could read my mind, because I was definitely feeling empty at that point.

In a few minutes, we were both almost there. The machine fucking him, my ass filled with a dildo, and each of our cocks in each other's mouths. His hairy musky smell was hot and erotic, and the taste of his precum was salty and sweet all at once. He soon began to jerk around and I knew he was going to go. I let myself feel all of the pleasure at once and began to edge with him. Like magic, through the jerking, stinky, sweaty, soaked motions of our hot fetishized fucking, we both released our loads at the same time. The drugs and pent up excitement made my orgasm something I had never experienced before. I was lightheaded and out of breath, but I had a cock to suck, so I kept on. He let loose what seemed to be a pint of his hot jizz. I let it fill my mouth and swallowed it all in one gulp. The load I had been saving was released in ten hot, long, salty ropes of cum. They hit the back of my master's throat and he coughed them up on my dick, but he sucked it all off the shaft and balls and swallowed every drop. 

We both slurped each other dry and laid there for a moment. The situation was intense and exhausting, but it had been one of the most explorative and wonderful nights of my life so far. The warden rolled off of me and stood up.

"You did great your first night," he said as he towered over me, still laying down, enjoying the moment. "You met every expectation I had, and then some. I'll send you down with Bryan and you can get cleaned up. You'll find your cell to be a bit bigger than the rest, with several amenities not afforded to the rest of the inmates. I expect you'll continue to earn those privileges."

"Yes, sir. I will. I promise."

"Good slut. You're dismissed."

I got up as Bryan walked in. The warden really ran a tight ship around here. He must have been waiting outside that door the whole time. He escorted me back to the room where we had our own romp just hours before. I took off my clothes, washed off my makeup, showered off and flexed my asshole to tighten myself up again.

"I trust you enjoyed your time with the warden," Bryan said.

"Yes I did. It was pretty intense. I've never experienced that before. It was so hot. I wish you were there, though. It would have made for a hot threeway. Or nineway, I suppose." 

"The warden doesn't like to fraternize with the guards. Those men were just random gigolos that he hires for his raunchy fantasies. You and I will have plenty of fun together during your stay, though. I'll get a few of the guards together and we'll all run through you soon enough."

"That sounds perfect. Thanks for everything, Bryan." He never said you're welcome to me. He just threw me some clothes and had me get dressed. He walked me down a secluded hallway with no rooms. At the end was a very comfortable room. A queen-sized bed with a real mattress, a television, a cable box, and even a menu for me to order anything I please. I was basically on vacation in here. All I had to do was swallow cock and cum in both ends of my body and I would be just fine. I couldn't wait to see what the next few years would bring.



The Warden and his Captive



{Disclaimer: this story contains a transitioned ftm - female-to-male gay character. However, it's not classified under "Transsexuals and Crossdressers", 

as the author sees this as a gay erotica story regardless. If this does not suit your tastes, please do not read further. If you -do-, enjoy yourself! ]     (



   He had been waiting there all night. 

The ice in his glass of rum and coke was mere slivers, the condensation along the outside a chill reminder of how long he had been sitting at the seedy bar. 

This wasn't Erik's scene. His pierced ears pounded with music that was far off from his tastes and although he was a smoker himself, 

nothing could remove the dry bitterness in his throat from the cloud that hung inside the building. 

His tongue played over the metal ring that ran through his full lower lip, his mind attempting to push past the shrill singer's voice and figure out why the 

hell he was here in the first place. 

   "It can't be all -that- bad, can it?" a deep baritone called out next to him. Erik rolled his hazel eyes, not even looking up to put a face to the voice 

as he responded loudly. 

   "I'm not a regular. And yes." He sighed, although he couldn't even hear himself do it. A strong hand on his shoulder finally made his eyes move from the 

ever-so-interesting alcoholic beverage. 

Erik was never an intimidating figure. At barely 5'8, with a slender but toned frame, he hadn't had a day since hitting 21 where he wasn't carded for smokes or drinks. 

Perhaps it was the spiky mess of blond hair or the way he only had a small soulpatch of matching color beneath his pouting lips. 

But THIS man... 

He drank in the sight of this stranger and it intoxicated him faster than any shots in this place could. His sparkling eyes were brown with sparks of green around 

the edges. His dark brown hair was cropped and coifed with a part to one side, which complimented the look of the goatee that wrapped around his lips. He was taller 

by a few inches, but then again most men were, and although Erik could see the muscles in his upper body through the button shirt and traditional vest, his had 

enough weight on him to look healthy and content. 

   "Sorry lad, did you want me to leave you be?" 

A shake of his head brought him out of his momentary trance, giving a nervous chuckle in attempt to break the awkwardness of what he had been doing. 

   "No, please stay. Forgive me. The name's Erik," he rattled out quickly, offering a hand to the other male. Upon looking down, he saw that the man 

was leaning on a cane, favoring his right leg. He shifted slightly to accept the gesture of greeting. 

   "Call me Ward if you'd like. A pleasure, Erik." 

Something struck him, even though it was against most everything he believed in. He wanted to fuck this guy, and to hell with what he knew of him besides his name. 

With a gulp and a surprised look from the new acquaintance, Erik chugged down the last of the flat drink and grinned. 

   "Can we get the hell out of here?" 





   "I need to fuck you...-now-." 

Ward's hand ran up Erik's chest and tugged hard at the fabric with a lust that was met only by Erik himself. They were barely in the door of the man's apartment, 

and even though he was attempting to get his bearings in the dimly-lit living room, Erik's attention was pulled elsewhere. He felt the rock-hard cock under the 

tight jeans the man wore and blushed slightly, even as he moved to start unbuttoning his own shirt. Those gorgeous eyes on his flesh burned into him as he 

stripped off the fabric and quickly felt fingers sliding along his warm skin. Then lips...hot and needy across his collarbone and shoulder. It sent sparks 

throughout Erik's entire body but -fuck- did he want more. 

   "Is...did you want to..." was all Erik got out amidst low whimpers and moans, his body already trembling with nerves and excitement. Ward roughly stuck 

fingers into the top of Erik's jeans and lead him down the hall and into the master bedroom. 

   "Get on the fucking bed." 

Erik winced at the command, not used to being spoken to in such a manner but he did so regardless. The sheets felt cool against his warm back as he wriggled into 

place, with Ward abandoning his cane quickly to pin the smaller boy down by his wrists. A gasp of slight protest was enough to make the man's cock strain harder 

against the zipper and although Erik was cautious, he -needed- to be fucked. A shiver ran through his body as lips pressed and sucked hard against the tender skin of his neck. 

   "Put your arms up, pet.." Ward cooed out softly, a contrast to his quick and forceful movements as he cuffed Erik's wrists to the bedposts. Sliding his fingers 

down the flat chest, if he had noticed the slightly raised scarring on Erik, Ward hadn't mentioned a thing. Erik's back arched to the touches, his hips gyrating up at 

his new lover. A chuckle emerged from the man's lips at this, tsktsk'ing. 

   "Seems you want something from me..." Ward unbuttoned the top of the jeans, letting his fingers tease the hipbones that emerged. "Tell me, pet, what exactly -is- it that you need?" 

A whine was all the response Erik could muster as the expert fingers moved lower, unzipping, playing in his dense pubic hair and lowering the material further. 





                    Silence. 



   "You're trans." 

It was a statement, not a question and Erik held his breath for what seemed like an eternity...until it was blown out to inhale a gasp as Ward's lips found the small cock nestled just below without another word said. Erik's lips tried to leak out words. 

   "Shut the hell up and let me blow you, Erik." 

It was the first time the man had used his name since the bar and it gave him a renewed sense of security. 

This guy knew what he was doing. His lips stroked perfectly along the engorged shaft, lustfully sucking up the juices that swarmed the area and Erik could do nothing but clench his fists in the restraints and rock his hips toward his lover's face. His leg muscles were tensing and the groans could not be held back as Erik neared explosion. 

   "Don't you dare come. You'll do that once my cock is buried in your tight little ass." 

Erik whimpered and tried desperately to remove himself from the man's hot mouth. A slap struck true across his cheek, although all motion did stop. 

   "You want something, you ask for it. Only -I- take what I want." Ward had moved himself up over top of Erik once more, and suddenly their hard cocks touched. Obviously despite himself, Ward let out a groan of pleasure at that, much to Erik's pride. He started grinding upwards but quickly stopped upon remembering his stinging face. 

   "Please fuck me. I need you inside me." Erik bit his lip shyly, now allowing his hips to raise and slide his cock against the pulsing one above him. God, how he 

wished he could reach out and stroke it...suck it...but the clacking sound the cuffs made against the headboard reminded him how futile his hopes were for that right now. 

   Perhaps not. 

Ward crawled his way up Erik's chest, straddling his face and carefully lowering his muscled ass down. Erik felt the man's tight but full sack against the bridge of his nose 

and breathing in the musky scent was enough to get his mouth watering. 

   "Prove it. Fuck -me- with that tongue of yours." 

Erik wasted no time dipping into that tight ring, his saliva drenching the hot skin and making his captor groan. He could hear the wet sound of Ward furiously jacking himself off 

above him and it drove Erik into a frenzy, tongue-fucking his lover with all the fury he wished -he- could be receiving from the man's cock right then. It was so warm, so inviting... 

   "Fuck...-fuck-" Ward cursed through clenched teeth, grinding himself down on Erik's face as he neared orgasm. Putting a hand out to steady himself on the headboard gave Erik just enough reach to grab the man's forearm. As if the gesture had spoken to him, all movement stopped in Ward's body. He laughed, lust-strained with a shake of his head. 

   "I guess I should save my load for you, hmm? Why waste my seed when it could be dripping out of your ass instead." 

He waited for no response as he moved himself into position between Erik's legs, reaching over to the nightstand nearby to squeeze warm lube onto his hard dick. 

  "Lift your legs, Erik..." 

Even as he did so, Erik felt Ward's hands press against the crook of his knee, pushing them closer to his chest and his ass into the ready. Jesus, was he ready.... 

It always hurts at first. 

Erik whined, not realizing just how thick a cock his captor had until this moment when it was 

forcing itself into his tight orifice. It felt hot and filling and it was precisely what Ward had been 

waiting for...lusting for... 

   "Light, you're fucking tight, pet. Fuck!" the man gritted out, even as he plunged himself in deeper. He wasn't satisfied until he was buried to the balls, and Erik enjoyed every inch of eight that he wrapped around like a glove. He licked his lips and gave a thrust toward his lover. 

    "Please fuck me. I need it. -Please-." Erik whimpered, playing up on his lust knowing full well there was no turning back for Ward now. Another slow thrust drew a gasp of ecstasy. "Fuck me, damn it!" 



   It was the point of no return. 

Erik cried out loudly as the man pounded relentlessly into his ass, each thrust bringing him balls-deep. They smelled of sweat and sex and both were driven crazy in the heat of the moment, rocking and fucking together in rhythm. Ward released his grip on Erik's legs, letting them rest on his shoulders as he plowed himself in and out of his sextoy, pressing down enough to suck one tender nipple on Erik's chest before working his way up to his mouth and neck. 

   "Please...please..." Erik yelped, his nails nearly breaking the skin on his palms as he neared coming with each forceful thrust. Ward tugged gently on Erik's lip ring with his teeth before whispering in the lad's ear. His voice was ragged and bitter. 

   "You want to come? You want to come, pet?" 

Nodding was the only response and another slap rung out as Erik received punishment for not speaking up which brought out an unexpected shock as the boy cried out like a wailing child, his taut muscles squeezing down on Ward's cock while the orgasm rode out. 

   "You...little fucking..." was all that escaped the captor's lips before he shot his thick sticky load inside the hot tunnel he had been fucking, his body convulsing above Erik as he spurted the last of his orgasm and fell panting on his chest. 

Erik caught his breath and laughed to fill the silence as they laid there - a soaking, sticky hot mess. 

    "Best shot I had all night." he said with a corny grin. 

Ward chuckled and patted his chest. 

   "Same time next week then?" 

Erik raised an eyebrow, looking over at his new lover.

   "Sure thing. Next time -you- wear the cuffs." He smirked. Ward sneered, but only halfheartedly, putting the key to the restraints and pulling the skinny boy to his chest.

   "Nice try, lad. Nice try,"



The Warden and the Prisoners



After the US Congress repealed the constitutional separation of church and state, the United States officially became a Christian Nation. One of the consequences of this change has been the severe crackdown on sexual activity in prisons. Even masturbation is now forbidden, and severe punishment is rendered to offenders who fail to control their sexual impulses.

Warden Ray takes seriously his responsibility to enforce the ban on all sexual activity. He believes masturbation is particularly offensive, and requires all inmates, both male and female, to wear electronic sensors that alert guards if they begin to masturbate.

Inmate M4932, a male, and inmate F3570, a female, are incarcerated for the crime of apostasy against the Christian Nation. By coincidence, on the same evening at the same time, in their bunks in separate areas of the institution, M4932 and F3570, who had been in prison for several months, could not bear their sexual frustrations any longer and began to masturbate. Within seconds, and before either could reach orgasm, guards showed up, yanked them from their beds, and took them into custody. Each one was escorted to the Sexual Purity Office for punishment and Christian re-education.

Warden Ray liked to take a personal hand in punishing masturbation offenders. This night he felt particularly zealous in his mission to teach M4932 and F3570 a lesson in self-control.

Warden Ray instructed guards to bring the offenders to Sexual Re-education Room #5 where he would personally administer their correctional training. The room was furnished only with a king-size bed with shackles at each corner. Once he and the two offenders were in the room, he locked the door behind him. He resolved to teach them a lesson they would not soon forget. 

Warden Ray stated the rules for their treatment: 1) You will do what I say, no questions asked. 2) You will not speak unless I ask you a question, except as follows: a.Because the law prohibits physical injury of inmates, each of you will have a “safe word” that you may use when physical pain becomes unbearable. b.You must announce when you are nearing orgasm. Neither of you may have an orgasm unless I allow it. 3) You will not look at my face, and you may not look at each other’s faces. 4) You will call me “Sir”, as in “Yes, Sir” and “No, Sir” 5) Female is responsible for keeping Male’s cock hard at all times so as to maintain his sexual frustration. Any violations of these rules will result in appropriate punishment.

He blindfolded both M4932 and F3570, whom he called simply “Male” and “Female.”  Once blindfolded, Warden Ray ordered them to strip naked - he stripped also. He then handcuffed each inmate with hands behind their backs, and ordered them to stand with legs spread wide apart. He lightly slapped and teased their private parts with his baton, taunting them with comments like, “So, you’ve been fantasizing about the opposite sex, eh? Well, I’ll stop that. When I’m finished with you two, you’ll have no more fantasies.”

Warden Ray then instructed Female stand directly in front of Male and to twist her torso rapidly back and forth, rubbing her breasts across Male’s chest, while the Warden fingered her pussy between her wide-stretched legs. While continuing to finger-fuck her, he told Male to sit on the edge of the bed and for her to straddle his legs and bring her breasts to his face so he could suck her nipples. Warden Ray instructed Male to slowly and gradually bite down on each nipple hard enough to cause her to say her safe word.

After a few minutes, he instructed Female to get down on her knees and suck Male’s cock until it became fully erect and throbbing with desire. Then he instructed Female to abandon Male’s cock, and to suck his own while Male remained helpless, only able to hear the slurping sounds of the Warden Ray’s cock being sucked. Of course, Warden Ray could have orgasms any time he wished, while Male and Female were denied their pleasure.

After awhile, Warden Ray said to Female, “Because I’m a man and not homosexual, I can’t personally punish Male the way he must be punished. So, I’m going to force you to do it for me, under my direct and close supervision.” He removed Male’s handcuffs and instructed him to lie on the bed on his back, and shackled his wrists and ankles to the four corners. 

“The method of this training is to use the unbearable intensity of your own sexual desire as your punishment. I’m going to make you both so horny that you’ll beg for release. But neither of you may have an orgasm unless I allow it. I am forbidden by law to injure you physically, but you’ll wish for physical punishment instead of the sexual punishment you’ll be suffering tonight.”

Warden Ray ordered Female to suck Male’s cock until he came close to orgasm, while he himself fondled and finger-fucked her. Then he said, “Now it’s time to demonstrate the two methods of control of Male’s sexual impulses.” 

First is the ball-squeeze technique. Ordering Male to spread his legs wide and bend his knees slightly, so his cock and balls are exposed and vulnerable, Warden Ray explains or demonstrates how Female must grip Male’s balls in one hand, thumb and forefinger forming a tight circle around his upper scrotum. She then slowly and gradually increases pressure until he is forced to say his safe word. While she tests this technique, Warden Ray makes her suck his own cock, taunting Male by pointing out that he is getting his cock sucked while Male’s balls are being crushed. Warden may make Female test the ball-squeeze technique on Male several times as he enjoys having is cock sucked, justifying it as necessary training for her to learn the correct amount of pressure that may be legally applied. If Male’s cock softens due to the pain of her abuse of his balls, Female must pump it back to full size.

Second is the “advanced orgasm control” (AOC) technique. He instructs Female to form a tight circle with the thumb and middle finger of one hand around the top of Male’s scrotum, his balls in her grip and pulled slightly down and away from his body. She then is told to hook the forefinger of the same hand around the base of his cock. By clenching her fist tightly in this position, she will be able to sense two signals of Male’s impending ejaculation: 1) His balls will retract toward his body. 2) His cock will harden at the base as semen begins to flow into it. Warden Ray instructs Female to test this technique by sucking Male’s cock until he nearly ejaculates, then stopping when she senses these signals, leaving Male in an agonizing state of intense desire. He explains that there may be a delay of one or two seconds after she ceases to stimulate his cock before semen appears, so she must slow her sucking or stroking as he gets close.

While Male is lying helplessly in agonizing frustration after the AOC, Warden Ray removes Male’s blindfold and says, “Now I’m going to make you watch what you can’t have.” He removes Female’s handcuffs and instructs her to straddle Male on her knees and her hands braced on the headboard so her breasts are suspended over Male’s face while Warden Ray fucks her from behind, doggy-style. He pumps his cock violently into her, causing her breasts to sway and bounce tantalizingly just inches above Male’s face. Warden Ray continues fucking Female and taunting Male as long as he wants, having an orgasm if he wishes. He may allow Female to have an orgasm if she signals him that she is close, or he may deny it. In either case, Male can only helplessly watch Female’s delicious breasts hanging from above while his cock desperately needs release.

Then Warden Ray even further intensifies Male’s desperation by instructing Female to repeat the AOC several times, pausing for a minute or so between repetitions to let him “cool down.” During these pauses Male is forced to suck and bite her nipples, which she suspends above his face. While Female is torturing Male with repetitions of the AOC, Warden Ray uses her body for his own pleasure in any way he wants, by fucking her, eating her pussy, or fondling her. He continues to taunt Male by pointing out that he is happily fucking Female while Male is in intense and ever-increasing sexual frustration.

After awhile Warden Ray tells Female to slide Male’s cock into her pussy, but only by an inch or two. Male must remain completely motionless - if he tries to thrust into her, she must take him out and do the ball-squeeze punishment. If he is able to remain motionless, Female will slowly lower her body so Male’s cock is completely inside her. Male remains motionless while Female speeds up her in-and-out motion for a while. Just as Male is approaching orgasm, Warden Ray abruptly commands her to switch to his cock, leaving Male helpless. Warden Ray thrusts Female vigorously as he fucks her, so Male can only watch her bouncing breasts, wishing desperately that he was fucking her instead. Warden Ray switches Female back and forth with Male a few times, and may himself have the orgasm that Male is denied.

Eventually, Warden Ray decides to torture Male even more severely with the “dry orgasm” technique. He instructs Female to stroke Male’s cock by hand and use the AOC until just one drop of semen emerges from Male’s cock. She then stops immediately, as he writhes in desperate desire for more stimulation to finish his orgasm. For this procedure, Warden Ray allows Female to remove her blindfold so she can watch for visual signals of impending ejaculation, such as swelling and darkening of Male’s cockhead, in addition to the two tactile signals that she has been practicing to perfection. After a pause of a minute or two, Female repeats this process, each time allowing only one more drop of semen to appear. Warden Ray cynically gives Male permission to ejaculate, knowing that he cannot do so as long as Female skillfully stops at just the exact second, a moment or two before the drop of semen actually reaches the tip of his cock. Each time Male’s orgasm is denied, Warden Ray taunts him by ordering him to watch Female suck his cock while Male is suffering extreme frustration of interrupted ejaculation.

Warden Ray incentivizes Female to use her utmost skill and sensitivity as Warden Rays’ instrument of torture of Male, allowing only a tiny drop of semen to appear with each AOC - the promised incentive is that Warden Ray will eat her pussy until she has all the orgasms she desires if she does a good job of torturing Male. When Warden Ray estimates that all of Male’s semen has been extracted, drop by drop, by the repeated AOC’s, he instructs Female to pump his cock vigorously by hand until he has an orgasm. If this torture has been correctly administered, his orgasm will be dry, with no more semen appearing.

Following Male’s dry orgasm, Warden Ray may fulfill his promise to eat Female’s pussy until she has all the orgasms she wants, or to fuck her as long as he likes. Male must simply watch as Warden Ray enjoys the pleasure of Female. 

After a period of time, Warden Ray instructs Female to impose one final punishment upon Male. She must suck and stroke his wilted and limp cock until it is again erect, then pump it as fast as she can move her arm. Male is forced to spread his legs and slightly bend his knees so his balls are exposed and vulnerable to Female’s rapid and brutal pounding. Warden Ray instructs her to grip Male’s cock in midshaft and pump rapidly, causing Male’s balls to flop wildly and slap against his body. If this abuse of his balls becomes unbearable, he may say his safe word, and Female must stop and suck Warden Ray’s cock a few minutes before resuming her abuse of Male’s balls. If Male can withstand the punishment of his balls long enough, he may have a second orgasm.

Upon completion of their Christian re-education, Warden Ray admonishes Female and Male to never masturbate again while they are inmates in his prison, or they will again be subjected to severe punishment by the Sexual Purity Office. 



The Warden of Cryosleep



"We'll sleep for two years?" Brandon Pace, the eager intern, couldn't hide his apprehension before his first interstellar flight. The crisp, white body suit enhanced his lithe and boyish frame that seemed far too young to be frozen in time.

"You won't notice it. You'll be asleep. It'll feel like a good night's rest, only when you wake up, we'll be at Proxima Centauri." Dr. Alice Hill tried her best to comfort the teen, but she had plenty of work to see to before the chambers were sealed within the hour. She flipped a curl behind her ear and set to recording the readings from his monitor. 

"You and Ramsey will be alone all that time?" At mention of the engineer, Alice couldn't help but glance across the room at him. Brandon made it sound like a bad thing. 

"Yeah, that's the way it works on long flights," she replied absently, jotting down his numbers and ready to move on.

"So, you'll be two years older when we get there?" 

She couldn't resist the genuine curiosity inlaid with total fear. "Yep, you three get to stay forever young while the engineer and I continue aging. Feel better?" 

"Yeah, thanks Dr. Hill." He smiled so wide she almost felt guilty she'd slowly kill his brain over the next two years.

"Sure thing, kid." Satisfied he would survive for the next ten minutes without her, Alice moved on to the next cryo chamber, the one belonging to the ship's captain. 

"This is your fifth trip in cryo?" she asked to make sure she had it documented correctly. 

Villareal nodded in his quiet way, the plentiful muscles rippling under his shirt despite the small movement. She wondered if such a tight shirt would get uncomfortable after two years under. Heart rate. Body temperature. Respiration rate. She scrawled the numbers from the leads and moved on to the next, careful not to stare too long.

At thirty-one, Villareal was one of the oldest people to undergo cryo for IGEA in the last five hundred years. Preference was given to younger candidates, but the captain's experience in flight and his excellent physical condition were enough to keep him on the table for future assignments. They were lucky to have him. 

As she reached the final patient, she found Dr. Browning firing off a list of very specific instructions while Weston Ramsey, the engineer, did his best to keep up. "If you get a luminosity reading over 10%, you need to wake me. Or if the computer picks up another planet once we're past the Alphas."

"Sure, sure." Weston attempted to appease the astrobiologist, but there wasn't much he could do. Hudson Browning would only be satisfied by a fully awake flight to the red dwarf. 

"Alright, Dr. Browning. I need you to finish up and go ahead and lay down. You want the best possible numbers before we launch." Alice kept her voice calm and smooth, which she had learned helped relax the sleepers before going under.

The reminder of the imminent departure was enough to shock him into obedience. He was a few years older than Alice, but she had already earned her position and then some. 

After double checking all the readouts, tapping the leads to assure they remained attached, and checking the men's positions in the chambers, she decided the time had come. 

"Alright, gentlemen. Lids are going to drop. The gas will fill the chamber and you'll drift to sleep like a baby. With any luck, you won't wake until Proxima Centauri. Happy dreams, gentlemen."

She checked one last time to make sure they were all properly positioned and the leads were still getting good readings. Alice pressed the button that lowered the three glass panes onto the chambers with the gentle hum of rushing air. Inside, a milky gas swirled until their faces disappeared in the fog. A quick glance at the monitors confirmed each was already asleep. 

"Kind of freaky when you watch from this side," Weston offered when a permeating quiet filled the room. 

"I guess so. Seems normal to me." Her eyes never moved from the sheets as she filled in the numbers.

"Have you ever been in cryo?"

"Oddly enough, I haven't."

"So, you're the resident expert of cryosleep and you've never done it?" While his question was rather accusatory, she couldn't hold it against him. An easy smile occupied his angular jaw and she was useless to resist his charm.

"How am I going to keep everyone alive if I sleep on the job?" She smiled and tapped his ribs with an elbow before turning down the corridor. There were only thirty minutes left to report any problems with the monitor feeds before launch. 

Just two doors down, she sat in the plush office chair and clicked on the wall of screens. Each of the three men occupied their own panel. A live video feed hummed alive on the left half of each rectangle and the leads readouts on the right. The red, green and blue lines darted up and down as the system hummed to life. It would be her instrument to keep the three men alive for the next two years. 

A few minutes into documenting the initial readings for each man, the intercom screen beeped twice and illuminated, revealing the stone face of her supervisor, Dr. Nobbert, in front of a screen bearing the Inter-galactic Exploration Agency logo. 

"Afternoon, Dr. Hill. Is Ramsey there with you?"

"No, sir. I left him at the cryo chambers just a bit ago. If you'll wait just a minute, I'll find him." The ship was much too large to search in such a short time, but she didn't want to appear as if she didn't have everything under control. While Villareal was asleep, she was in command of the expedition. 

"I'll try him on the bridge," he said in decline. A half second later, Dr. Nobbert's bird-like face shared the screen with the hazel eyes and tousled blonde hair of the engineer; a comparison that did no favors for her supervisor. Her own heart-shaped face and dark curls appeared in miniature in the top right corner.

"All systems are ready for launch. How do things look on your end?" their supervisor asked of Ramsey.

"Engines are fired up and ready to go. I triple checked the coordinates in the Nav. Life support systems, anti-gravity regulators, and oxygen equalizers are all fully operational. We're all set up here." Weston sounded surprisingly professional, a stark contrast to his casual appearance. 

It would be a lie to say she hadn't considered him sexually, that she wasn't attracted to his muscles and his cool demeanor. In reality, they would probably end up sleeping together before their arrival in deep space. Back in the day, little care was given to the crewmembers selected to make the journey awake, but the resulting gay and lesbian relationships amongst otherwise straight individuals resulted in a new level of care. She'd been given the power to deny his position, just as he'd been allowed to do for hers.

"And Dr. Hill?" Nobbert's voice brought her eyes back from the daze. 

"All three are down and looking good. We're cleared for launch."

"Alright, I'll give them the go-ahead. We'll check in with you in thirty days. Good luck." Without pretense, the left screen darkened so that only Weston's picture remained, but it, too, went dark a moment later. 

Thirty days. It was now an arbitrary concept. Without the constant, artificial spinning of the Gamma Outpost-their home for the last three months-mornings would merge into nights and afternoons might disappear entirely. The ship would create a false sense of time to suit their biological need for regularity, but it was just a mirage, a matrix to pacify.

Along with the blur of time, they would have to contend with the loneliness and the silence. On the other hand, Dr. Hill was no stranger to the eerie quiet of deep space. As the primary cryogenics officer, it was her duty to monitor the passengers in cryostate until they reached their destination, this time the nearby star Proxima Centauri. As the ship maneuvered from the port and entered hyperdrive, there was the palpable shift in the atmosphere that marked the beginning of their long journey. 

"Hey Doc. How about a drink to celebrate?" Ramsey appeared in the doorway. 

"Celebrate?" she asked. 

"Yeah, you know. We just launched on a major flight. I think that deserves a drink. You look like a wine sorta girl." Without waiting for a response, he disappeared down the corridor. 

Guffawed at his assumption, Alice Hill dropped her clipboard roughly on the desk and followed him. Arriving at the galley, she stated pragmatically, "I happen to enjoy a good bourbon."

"Well, that explains the storeroom. There's enough bourbon to kill an elephant," he replied as he poured a beer into a frosted mug. 

"What do you know of elephants?" she asked, surprised he'd even heard of such a thing. 

"They were an animal, pretty big one, right?" The wind flew right back out of her sails. It had been too much to hope. 

"Uh, yeah. Pretty big." Deflated, she turned to head back to her office. 

"Doc, didn't you want a drink?" 

"No, I'm fine. Thanks." She didn't even bother to turn her head as she spoke, a bad habit of hers. 

"Did I somehow manage to offend you in the first ten minutes of our flight?" His candidness appealed to her and she found herself turning to address him. 

"I'd hoped you appreciated the old ways, but not many do anymore. It was my mistake."

"So, it's true. You're an antiquarian. I guess with a name like Alice you'd have to be." Engineer Weston Ramsey wasn't the first to comment on the seldom-used moniker. Symbolism in names disappeared long ago, along with other romantic fantasies. 

"It was a book. My mother loved books." It was all the explanation she could offer of her childhood in paradise. It would seem like torture to the rest of the galaxy, but for her, it was an inexplicable utopia. She would always be drawn to the ways of the old world. Again, she left to return to her office. 

Alice didn't have another run in with the engineer for two more days. The ship was large enough to let each of them get lost in their own space. Before she died, Evelyn Hill had filled a digital reader with all the books she considered must-reads. Finding a power source for such an outdated device was a challenge, but it was amongst Alice's most prized possessions. She was well into Sense and Sensibility when Weston's blonde mess appeared. 

"You like chess?" he asked with no attempt at a greeting. He wore baggy sweatpants and a tee shirt that was just a little too tight for his generous muscles.

"As it happens, I do." 

"Is that how people used to talk?" Weston's smile twisted at the words. 

"As it happens, it is," she teased, pleased when his usually handsome face twisted again. 

"Alright, well the board's set up in the galley if you're interested." 

"Sure," she replied, pleasantly surprised at his interest. Her bare feet plodded quietly down the hall behind him. 

The living spaces of the ship were complete with a fully functional kitchen, dining area, and recreational room. Entering the kitchen, she saw a use for the space the original designers had probably never anticipated. Atop the large hexagonal table, a chessboard appeared via the holographic projector. "Oh," she let slip before she could help it. 

"I'm sorry. I figured you'd like to play with a physical board but there isn't one on the ship." 

"You checked?"

"Yeah, what do you think I've been doing for the last two days?" As if it were a perfectly normal thing to say, Weston sat in front of the white pieces projected on the table. Already, a beer and bourbon sat at their respective positions.

"But- You didn't know I would want to play."

"Well, there's plenty of time to learn. We have two years together, remember?"

"Now that you mention it, I do recall something about it." Both laughed as she slid into the opposing chair and pulled back her dark curls in preparation for the game. Already, his calm permeated the space and let her relax. With high hopes, Alice wondered how long it would take to get to the sex after all. 

"Pawn to E-three." Weston indicated his desired move quickly, a little too quickly. Alice immediately pegged him as a novice but would take her time in destroying him. There would be time to train him up and then some. 

"Pawn to E-five," she offered in response. 

"Bishop to B-five." Alice had to sit back in her chair and admire the bold move from such a beginner. 

"Someone's been practicing."

"There's not much in the system at the advanced levels, but enough to get started." 

The cryogenist let her thoughts fall to the game and the predicament she found herself in far too early in the game. Already, Weston pinned half her pawns, rendered her rook, bishop and knight useless, and set up a move to kill the king in two turns. She had no choice. "King to E-seven."

When Weston smiled at her move, she knew she was in trouble.

"Knight to B-three. What's the book?" he asked as he adjusted the bulky black watch that was so fashionable this year.

"What book?"

"The book you were named for. You said your mom liked books."

"Oh, yeah, she did. Alice's Adventures in Wonderland by Lewis Carroll." After a moment of marveling at his questions, she remembered the game. "Pawn to H-five."

"What kind of adventures did she have?" he seemed interested in her answer but his eyes never moved from the holographic board. 

"Well-" Alice had always struggled to rationalize the fictional novel out of context. If someone wasn't familiar with it, the story sounded pretty far-fetched. "She follows a white rabbit down a hole and meets all sorts of strange characters: a mad hatter, an odd set of twins, an evaporating cat. Eventually, she battles the evil queen. It's a lot of nonsense but there's logic, too." 

"Sounds pretty neat. Do you have a copy with you?"

"Uh, yeah, I do." She made no attempt to hide her surprise. 

"Would you mind if I borrowed it?"

"No, I guess not." In fact, she would mind. She would mind very much. Her physical, paper copy of Alice's Adventures was one of the last. The thought of lending it out terrified her. "Can I ask you something?"

"Go ahead."

"Why are you doing all this? You aren't really interested in reading a two thousand year old book. Are you?"

"People still read the Bible and it's way older than that. Besides, it's obviously important to you."

"Okay..."

Looking up from the projection, Weston's gaze bored right into her. "It's important to you, so I'd like to learn more about it."

"Alright." She composed a calm façade while her insides were threatening escape. The words didn't make sense coming from the guy she planned on having very casual sex with to save her sanity over the next two years. 

"Look, we got to select each other right? If we weren't compatible to live onboard together, this flight would have been doomed to failure. That's why our input was part of the selection process."

While the words he spoke were true enough, she couldn't imagine how they related to the current conversation. Nobbert had given her a list of twenty-five possible candidates with the understanding she would choose from the top two or three. After the first two declined, she picked Weston Ramsey, an insipid eighth, but something about him had caught her eye. When he had been given the opportunity to decline working with her, whatever his reasons were, he was the first to accept. 

Her face must have revealed some of her inner fluster; he stood up and walked over to stand beside her chair. "Do you mind?"

"Mind what?" The words slipped past her lips just before he pressed his own against them. Close up, she could smell the beer on his breath and the musty odor of man. Despite herself, she inhaled deeply, drawing in his air and collecting strength for her uncustomary reaction. 

Alice reached a hand up behind his neck and let her fingers dart between strands of blonde waves. The rough hand of her associate crawled down her back, pausing briefly along her lower back before reaching farther. A quick flex of his muscles was all it took to lift her out of the chair and plant her hips against his. Alice wrapped her strong legs around him to keep from falling. 

Amidst the chaotic rovings of tongues and mouths, she was vaguely aware of his legs pumping beneath them, traveling quickly down the sterile corridor. Her arms remained locked around his neck in eagerness and vertigo. 

Before she'd had her fill of his taste, her spine collapsed into soft fabric as he pulled away. Eyes darted around to take in her surroundings: bare walls, simple color scheme, a decorative approach that could only belong to a man. 

From across the room, Weston cued the lights to dim before hurrying back to her. His hips arrived just between her legs as he bent to kiss her again. Alice let her arms return around his neck to bring him in that much closer.

If that were as far as it had gone, she would have been satisfied. The engineer was a more than capable kisser and the strength of his arms didn't hurt his case. As a career driven woman, she had already tasted more than she could have hoped so early in their time together. When he began to pull at the edge of her shirt, the breath caught in her chest. 

It wasn't the way it was supposed to go. They were supposed to pretend like they didn't know they'd eventually sleep together out of sheer lack of options, play coy in the galley, and drop hints for a while. It was supposed to take months to get to this point, not a few days. He was going way too fast. 

Weston ignored the buttons that lined the front of her vintage top and hastily pulled the green plaid fabric over her head. Only a simple black bra and khaki shorts remained and, though she wasn't particularly modest, she found herself attempting to cover her chest with an arm. 

"Don't," he whispered close to her ear before his lips returned to hers. A brawny hand pulled against her wrist and slid it up above her head where he pinned it onto the bed. To her surprise, kisses landed in a line from her mouth up to her ear, then down her neck to rest just between her bra-clad breasts. A wave of goosebumps stippled her light skin where his lips touched her. 

Weston's rapid breath spread across her chest rousing an excitement she hadn't experienced in years. When his free hand lowered to work at the buckle of her brown leather belt, she began to realize where things were likely headed. 

Needing to make a decision, Alice knew she really only had two options: reject him and live alongside him for another two years or give in to the experience and deal with the consequences later. In truth, she couldn't find a reason to turn him away other than the unexpectedness of his actions. The bulge in his pants pressed between her legs was all the motivation she needed to make peace with it. 

As the buckle fell away, Weston moved both his hands to tug on the legs of her shorts and slide them off. The narrowed eyes of the engineer swathed over her body as he lightly stroked the tops of her thighs. "Shit, Alice, Dr. Hill, I just-I had no idea..." He gave up on his jumbled words and dove back in for a kiss, softer this time, and planted his hands on the sheets at either side of her flushed cheeks. 

Alice could only tighten her legs around his waist and take in the capable man she found pressed on top of her. Eager lips pulled away and landed just below her ear, sucking fervently. In the past, she would have protested any mark he was surely making, but in the depths of space, there was no one else to see. Yielding to his strength and hunger; she had no doubt that he wanted her. 

Giving in to the experience, Alice blindly felt along his muscled torso until she reached the elastic band of his navy sweatpants. Grateful of their lack of structure, she pulled them down easily until they caught and refused to move farther. 

The capable cryogenist felt suddenly inept when she couldn't operate a simple pair of pants, pushing onto an elbow to see what prevented her motions as Weston continued pulling against the skin of her neck. Alice had to laugh when she saw the source of her troubles: a fully-firm cock.